HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from Hilton Head Island (HHH) to Chicago (CHI) from $213

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
HHH — CHI
May 19 — May 261
From?
To?
Sun 5/19
Sun 5/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Cheap flight deals from Hilton Head Island to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Hilton Head Island (HHH) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 14, 2024.

Round-trip from

$223
From Hilton Head Island to Chicago (CHI)
Search Deals

What is the cheapest day to fly round-trip from Hilton Head Island to Chicago?

Flights from Hilton Head Island to Chicago are found to be more expensive on Thursday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

When is the cheapest time to fly from Hilton Head Island to Chicago (HHH - CHI)?

When flying from Hilton Head Island to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 43% versus a flight in the morning.

Cheap American Airlines flights from Hilton Head Island to Chicago

Explore cheap flight options specifically provided by American Airlines for the route between Hilton Head Island and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
Take a peek at the cheapest American Airlines flights we've detected traveling from Hilton Head Island to Chicago. Make sure to double check the flight details before booking.
Sat 9/144:18 pmHHH - ORD
1 stop3h 50mAmerican Airlines
Wed 9/185:30 amORD - HHH
1 stop5h 56mAmerican Airlines
Deal found 5/13$291
Sat 9/144:18 pmHHH - ORD
1 stop3h 50mAmerican Airlines
Wed 9/188:20 amORD - HHH
2 stops6h 30mAmerican Airlines
Deal found 5/13$300
Fri 7/262:41 pmHHH - ORD
1 stop5h 54mAmerican Airlines
Mon 7/295:28 amORD - HHH
1 stop5h 12mAmerican Airlines
Deal found 5/12$381
Tue 7/306:26 pmHHH - ORD
1 stop6h 33mAmerican Airlines
Thu 8/19:45 amORD - HHH
1 stop7h 11mAmerican Airlines
Deal found 5/13$431
Sat 9/1412:48 pmHHH - ORD
2 stops5h 57mAmerican Airlines
Wed 9/188:20 amORD - HHH
2 stops6h 30mAmerican Airlines
Deal found 5/13$449
Tue 7/306:26 pmHHH - ORD
1 stop6h 33mAmerican Airlines
Thu 8/15:00 amORD - HHH
2 stops8h 11mAmerican Airlines
Deal found 5/13$470
Fri 7/262:41 pmHHH - ORD
1 stop5h 54mAmerican Airlines
Mon 7/295:00 amORD - HHH
2 stops8h 11mAmerican Airlines
Deal found 5/12$605
Fri 7/2612:11 pmHHH - ORD
2 stops8h 33mAmerican Airlines
Mon 7/295:00 amORD - HHH
2 stops11h 56mAmerican Airlines
Deal found 5/12$705
Tue 7/3012:11 pmHHH - ORD
2 stops6h 33mAmerican Airlines
Thu 8/16:00 amORD - HHH
2 stops7h 11mAmerican Airlines
Deal found 5/13$718

Cheap Delta flights from Hilton Head Island to Chicago

Explore cheap flight options specifically provided by Delta for the route between Hilton Head Island and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
Some of the lowest-priced Delta flights we've found at this time heading from Hilton Head Island to Chicago. Ensure the flight price, dates, time, and airline match your criteria before you book.
Tue 8/271:15 pmHHH - ORD
1 stop7h 33mDelta
Wed 8/286:00 amORD - HHH
2 stops9h 43mDelta
Deal found 5/13$443
Tue 8/271:15 pmHHH - ORD
1 stop4h 30mDelta
Wed 8/289:30 amORD - HHH
1 stop6h 13mDelta
Deal found 5/13$463
Tue 8/271:15 pmHHH - ORD
2 stops8h 56mDelta
Wed 8/286:00 amORD - HHH
2 stops9h 43mDelta
Deal found 5/13$478

Hilton Head Island to Chicago 2024 flight deals

Discover exclusive flight deals for travel between Hilton Head Island and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
The lowest fares we've come across on flights traveling from Hilton Head Island to Chicago in May and June 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Sat 9/144:18 pmHHH - ORD
1 stop3h 50mAmerican Airlines
Wed 9/185:30 amORD - HHH
1 stop5h 56mAmerican Airlines
Deal found 5/13$291
Sat 9/144:18 pmHHH - ORD
1 stop3h 50mAmerican Airlines
Wed 9/188:20 amORD - HHH
2 stops6h 30mAmerican Airlines
Deal found 5/13$300
Fri 7/262:41 pmHHH - ORD
1 stop5h 54mAmerican Airlines
Mon 7/295:28 amORD - HHH
1 stop5h 12mAmerican Airlines
Deal found 5/12$381
Tue 7/306:26 pmHHH - ORD
1 stop6h 33mAmerican Airlines
Thu 8/19:45 amORD - HHH
1 stop7h 11mAmerican Airlines
Deal found 5/13$431
Tue 8/271:15 pmHHH - ORD
1 stop7h 33mDelta
Wed 8/286:00 amORD - HHH
2 stops9h 43mDelta
Deal found 5/13$443
Sat 9/1412:48 pmHHH - ORD
2 stops5h 57mAmerican Airlines
Wed 9/188:20 amORD - HHH
2 stops6h 30mAmerican Airlines
Deal found 5/13$449
Tue 8/271:15 pmHHH - ORD
1 stop4h 30mDelta
Wed 8/289:30 amORD - HHH
1 stop6h 13mDelta
Deal found 5/13$463
Tue 7/306:26 pmHHH - ORD
1 stop6h 33mAmerican Airlines
Thu 8/15:00 amORD - HHH
2 stops8h 11mAmerican Airlines
Deal found 5/13$470
Tue 8/271:15 pmHHH - ORD
2 stops8h 56mDelta
Wed 8/286:00 amORD - HHH
2 stops9h 43mDelta
Deal found 5/13$478

One-way flights to Chicago from Hilton Head Island

Search for one-way flight options from Hilton Head Island to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
Take a look at some of the best available options we've come across on one-way flights from Hilton Head Island to Chicago. Users needing a return flight from Hilton Head Island to Chicago should utilize the search form above.
Fri 8/26:26 pmHHH - ORD
1 stop6h 33mAmerican Airlines
Deal found 5/13$213
Fri 9/611:18 amHHH - ORD
2 stops9h 22mAmerican Airlines
Deal found 5/13$282
Sat 6/153:26 pmHHH - ORD
1 stop16h 47mAmerican Airlines
Deal found 5/13$340
Sat 6/153:15 pmHHH - ORD
Nonstop2h 37mUnited Airlines
Deal found 5/13$344
Fri 8/22:41 pmHHH - ORD
2 stops10h 05mAmerican Airlines
Deal found 5/13$353
Sat 6/1512:59 pmHHH - ORD
2 stops9h 04mDelta
Deal found 5/13$464

Find flights from Hilton Head Island to Chicago within your budget

Customize your flight search to find flights from Hilton Head Island to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$291 - $478

Route

Depart

Return

Price

Hilton Head IslandChicago O'Hare Intl

HHH - ORD

HHHORD

Hilton Head Island

Sat 9/14

1 stop3h 50m

Chicago O'Hare Intl

Wed 9/18

1 stop5h 56m

$291

Hilton Head IslandChicago O'Hare Intl

HHH - ORD

HHHORD

Hilton Head Island

Sat 9/14

1 stop3h 50m

Chicago O'Hare Intl

Wed 9/18

2 stops6h 30m

$300

Hilton Head IslandChicago O'Hare Intl

HHH - ORD

HHHORD

Hilton Head Island

Fri 7/26

1 stop5h 54m

Chicago O'Hare Intl

Mon 7/29

1 stop5h 12m

$381

Hilton Head IslandChicago O'Hare Intl

HHH - ORD

HHHORD

Hilton Head Island

Tue 7/30

1 stop6h 33m

Chicago O'Hare Intl

Thu 8/1

1 stop7h 11m

$431

Hilton Head IslandChicago O'Hare Intl

HHH - ORD

HHHORD

Hilton Head Island

Tue 8/27

1 stop7h 33m

Chicago O'Hare Intl

Wed 8/28

2 stops9h 43m

$443

Hilton Head IslandChicago O'Hare Intl

HHH - ORD

HHHORD

Hilton Head Island

Sat 9/14

2 stops5h 57m

Chicago O'Hare Intl

Wed 9/18

2 stops6h 30m

$449

Hilton Head IslandChicago O'Hare Intl

HHH - ORD

HHHORD

Hilton Head Island

Tue 8/27

1 stop4h 30m

Chicago O'Hare Intl

Wed 8/28

1 stop6h 13m

$463

Hilton Head IslandChicago O'Hare Intl

HHH - ORD

HHHORD

Hilton Head Island

Tue 7/30

1 stop6h 33m

Chicago O'Hare Intl

Thu 8/1

2 stops8h 11m

$470

Hilton Head IslandChicago O'Hare Intl

HHH - ORD

HHHORD

Hilton Head Island

Tue 8/27

2 stops8h 56m

Chicago O'Hare Intl

Wed 8/28

2 stops9h 43m

$478

Flights are sorted by cheapest first

Deals found on 5/13

When is the cheapest time to fly from Hilton Head Island to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Hilton Head Island to Chicago. Price data was last updated on May 12, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Hilton Head Island to Chicago flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Chicago by month

Plan your trip from Hilton Head Island to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Hilton Head Island to Chicago is currently $333 while a round-trip flight costs $412. Price data was last updated on May 12, 2024.

Currently, February is the cheapest month in which you can book a flight from Hilton Head Island to Chicago (average of $244). Flying from Hilton Head Island to Chicago in June is currently the most expensive (average of $342). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

January

$248

February

$244

March

$280

April

$258

May

$278

June

$342

July

$327

August

$274

September

$258

October

$248

November

$270

December

$248

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 14, 2024.
Read through reviews of airlines operating flights from Hilton Head Island to Chicago, such as American Airlines and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,706 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
10,706 reviews
Delta
8.0
Very good
10,706 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

United Airlines
7.4
Good
10,959 reviews
Delta
8.0
Very good
10,706 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

American Airlines
7.3
Good
14,561 reviews
Delta
8.0
Very good
10,706 reviews
Check prices

Food

7.4

Comfort

7.9

Crew

8.6

Entertainment

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Hilton Head Island to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Hilton Head Island to Chicago?

    For a flight from Hilton Head Island to Chicago, you will be flying from Hilton Head. Hilton Head Island (HHH) is just 3.3 mi from the center of the city. Hilton Head is the only Hilton Head Island airport and it handles 0 outbound flights to Chicago per day. 1 airline has flights to Chicago from Hilton Head Island on a regular basis.

  • Can I find flights from Hilton Head Island to Chicago for under $300 on Cheapflights?

    Yes, there are multiple flights from Hilton Head Island to Chicago for under $300. The cheapest flight booked recently is on American Airlines for just $291, but on average you can expect to pay $477.

  • What are the cheapest airlines flying from Hilton Head Island to Chicago round-trip?

    Cheapflights users have booked flights from Hilton Head Island to Chicago round-trip from $291. Another airline that can offer you cheap pricing is Delta.

  • What are the cheapest airlines to fly from Hilton Head Island to Chicago one-way?

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $213. However, be on the lookout for offers from United Airlines and Delta, as they are both options that can get you from Hilton Head Island to Chicago for a low price.

  • What are the most reliable airlines from Hilton Head Island to Chicago?

    Consider American Airlines (100%), Qatar Airways (100%) or Envoy Air (100%) when booking your flight. These represent the most reliable airlines when flying from Hilton Head Island to Chicago.

  • What are the cheapest flights from Hilton Head Island to Chicago?

    While on average a flight from Hilton Head Island to Chicago is generally $315, our data shows the cheapest flight currently is $222. When looking at the most popular route, (Hilton Head Island - Chicago O'Hare Intl), you can expect to pay $363 for that flight.

  • What does HHH to ORD mean?

    This is defined as Hilton Head Island Airport (HHH) and Chicago O'Hare Intl Airport (ORD). Codes like Chicago O'Hare Intl Airport are often used to just call airports uniquely. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Hilton Head Island to Chicago that include extra baggage allowance?

    The amount of baggage you can bring on your Hilton Head Island to Chicago flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Hilton Head Island to Chicago with specific airlines?

    Yes, Cheapflights allows you to browse and filter Hilton Head Island to Chicago flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Hilton Head Island to Chicago that include hotel bookings?

    Yes. In addition to deals on Hilton Head Island to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hilton Head Island to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hilton Head Island to Chicago.

  • Can I find deals for business class flights from Hilton Head Island to Chicago?

    Yes. Cheapflights offers flight deals from Hilton Head Island to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Hilton Head Island to Chicago that allow pets onboard?

    Many airlines flying from Hilton Head Island to Chicago offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Hilton Head Island to Chicago?

    Yes, you can often find last-minute deals on Hilton Head Island to Chicago flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Hilton Head Island to Chicago flight deals updated?

    The Hilton Head Island to Chicago flight deals you see on this page were last updated on 5/13.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Hilton Head Island to Chicago
See prices for flight routes from nearby airports that may be better suited for you.

Charlotte to O'Hare Intl flights
Charlotte to Midway flights
Charleston to O'Hare Intl flights
Savannah to O'Hare Intl flights
Charlotte to St. Louis flights
Columbia to O'Hare Intl flights
Greenville to O'Hare Intl flights
Charleston to Midway flights
Myrtle Beach to O'Hare Intl flights
Columbia to Midway flights
Charleston to St. Louis flights
Greenville to Midway flights
Savannah to Midway flights
Myrtle Beach to Midway flights
Greenville to St. Louis flights
Savannah to St. Louis flights
Columbia to St. Louis flights
Charlotte to Moline flights
Augusta to O'Hare Intl flights
Augusta to Moline flights
Charlotte to Evansville flights
Charlotte to Peoria flights
Charlotte to Rockford flights
Charleston to Moline flights
Myrtle Beach to St. Louis flights
Augusta to St. Louis flights
Charleston to Evansville flights
Hilton Head Island to O'Hare Intl flights
Augusta to Midway flights
Charlotte to Bloomington flights
Greenville to Bloomington flights
Hilton Head Island to St. Louis flights
Augusta to Bloomington flights
Greenville to Moline flights
Charlotte to Springfield flights
Greenville to Peoria flights
Greenville to Champaign flights
Greenville to Decatur flights
Greenville to Evansville flights
Columbia to Evansville flights
Columbia to Peoria flights
Florence to St. Louis flights
Charlotte to Champaign flights
Florence to O'Hare Intl flights
Charleston to Peoria flights
Columbia to Springfield flights
Myrtle Beach to Peoria flights
Myrtle Beach to Moline flights
Savannah to Peoria flights
Columbia to Bloomington flights

Top airline flying from Hilton Head Island to Chicago

Discover the top airline that operate flights from Hilton Head Island to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated May 14, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$195Average$325FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
New York to Atlanta flights
USA to Paris flights
Las Vegas to Hawaii flights
Kansas City to Orlando flights
Tampa to London flights
Chicago to Atlanta flights
Atlanta to Mumbai flights
USA to Kathmandu flights
Chicago O'Hare Intl Airport to Miami flights
Oakland, California to Las Vegas flights
Newark Airport to Punta Cana flights
Hilton Head Island to Ciudad Juárez flights

Search flights from Hilton Head Island to Chicago by cabin class

Find flights from Hilton Head Island to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to Montes Claros
Flights to Girona Costa Brava
Flights to Naxos
Flights to Bourgas
Flights to Hyannis Barnstable
Flights to Samos
Flights to Reggio Calabria Tito Menniti
Flights to Devils Lake
Flights to Ningbo Lishe Intl
Flights to Pellston Emmet County
Flights to Provincetown
Flights to Cortez Montezuma County
Flights to Ohrid
Flights to Oran Es Senia
Flights to Menorca/Mahon
Flights to Hakodate
Flights to Ordu/Giresun
Flights to Laayoune Hassan I
Flights to Cornwall Newquay
Flights to Melilla
Flights to Rennes St Jacques
Flights to Parikia Paros
Flights to Constanţa Mihail Kogalniceanu
Flights to Miyakojima Hirara

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Hilton Head Island to Chicago?

When you search for this flight from Hilton Head Island to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Hilton Head Island to Chicago?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Hilton Head Island to Chicago for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Hilton Head Island to Chicago with no change fees?

Yes, we can. To see specific flights from Hilton Head Island to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Hilton Head Island to Chicago become cheaper?

Of course! You can now track prices for flights from Hilton Head Island to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines